| UTR Pro Tennis Series Zadar | 2021/11/14 12:00 | Alen Rogic-Hadzalic v Ivan Penev | 6-3,4-6,6-2 |
| ITF M15 Sozopol | 2021/10/11 09:00 | Ivan Penev v Berk Ilkel | 6-7,6-1,8-10 |
| ITF M15 Sozopol | 2021/10/10 09:00 | Ivan Penev v Gianluca Coloma-Heck | 6-1,6-3 |
| ITF M15 Sozopol | 2021/10/04 07:00 | Yann Wojcik v Ivan Penev | 3-6,7-5,10-2 |
| ITF M15 Sozopol | 2021/09/13 10:30 | Tommaso Compagnucci v Ivan Penev | 6-2,6-3 |
| ITF M15 Sozopol | 2021/09/12 10:00 | Radu F Macovei v Ivan Penev | 4-6,3-6 |
| UTR Pro Tennis Series Sofia | 2021/09/01 11:00 | Samuil Konov v Ivan Penev | 4-6,6-1,6-0 |
| UTR Pro Tennis Series Sofia | 2021/08/31 06:30 | Martin Dimitrov v Ivan Penev | 1-6,6-3,6-3 |
| UTR Pro Tennis Series Zadar | 2021/11/14 13:00 | Vladan Tadic v Oleksii Osadchyi | 6-0,6-1 |
| Challenger Banja Luka | 2021/09/06 11:40 | Nikola Milojevic v Vladan Tadic | 6-0,6-3 |
| UTR Pro Tennis Series Portoroz | 2021/08/29 09:30 | Gal Emersic Potocnik v Vladan Tadic | 6-2,6-0 |
| UTR Pro Tennis Series Portoroz | 2021/08/28 08:30 | Denis Parshutin v Vladan Tadic | 6-4,1-6,3-6 |
| UTR Pro Tennis Series Portoroz | 2021/08/27 12:00 | Vladan Tadic v Volodymyr Uzhylovskyi | 5-7,2-6 |
| UTR Pro Tennis Series Portoroz | 2021/08/26 10:00 | Vladan Tadic v Domen Gostincar | 4-6,6-3,6-3 |
| UTR Pro Tennis Series Portoroz | 2021/08/25 10:00 | Nik Razborsek v Vladan Tadic | 1-6,4-6 |
| UTR Pro Tennis Series Portoroz | 2021/08/25 07:00 | Olexiy Kolisnyk v Vladan Tadic | 6-2,3-6,2-1 |